250. Jay-Z, 'Reasonable Doubt'

Roc-A-Fella, 1996

"The studio was like a psychiatrist's couch for me," Jay-Z told Rolling Stone, and his debut is full of a hustler's dreams and laments. It established Jay as the premier freestyle rapper of his generation and includes a filthy guest appearance from a 16-year-old Foxy Brown on "Ain't No Nigga."